An unusual radical smiles rearrangement

Eric Bacqué; Myriem El Qacemi; Samir Z. Zard

doi:10.1021/ol051568l

An unusual radical smiles rearrangement

Eric Bacqué
, Myriem El Qacemi
, Samir Z. Zard

Laboratoire de Synthèse Organique
Centre de Recherche de Vitry-Alfortville

Research output: Contribution to journal › Article › peer-review

Abstract

(Chemical Equation Presented) Radicals derived from N-(α-xanthyl) acetanilides or N-(α-xanthyl)acetylaminopyridines possessing a substituent next to the nitrogen undergo a hitherto undocumented Smiles rearrangement proceeding through a four-membered ring. It was also found that under certain conditions the amidyl radical produced by cleavage of the four-membered ring intermediate can undergo fragmentation to give an isocyanate. Such fragmentations are unprecedented at temperatures corresponding to refluxing benzene or chlorobenzene.

Original language	English
Pages (from-to)	3817-3820
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	17
DOIs	https://doi.org/10.1021/ol051568l
Publication status	Published - 18 Aug 2005
Externally published	Yes

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10.1021/ol051568l

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title = "An unusual radical smiles rearrangement",

abstract = "(Chemical Equation Presented) Radicals derived from N-(α-xanthyl) acetanilides or N-(α-xanthyl)acetylaminopyridines possessing a substituent next to the nitrogen undergo a hitherto undocumented Smiles rearrangement proceeding through a four-membered ring. It was also found that under certain conditions the amidyl radical produced by cleavage of the four-membered ring intermediate can undergo fragmentation to give an isocyanate. Such fragmentations are unprecedented at temperatures corresponding to refluxing benzene or chlorobenzene.",

author = "Eric Bacqu{\'e} and \{El Qacemi\}, Myriem and Zard, \{Samir Z.\}",

year = "2005",

month = aug,

day = "18",

doi = "10.1021/ol051568l",

language = "English",

volume = "7",

pages = "3817--3820",

journal = "Organic Letters",

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AU - Bacqué, Eric

AU - El Qacemi, Myriem

AU - Zard, Samir Z.

PY - 2005/8/18

Y1 - 2005/8/18

N2 - (Chemical Equation Presented) Radicals derived from N-(α-xanthyl) acetanilides or N-(α-xanthyl)acetylaminopyridines possessing a substituent next to the nitrogen undergo a hitherto undocumented Smiles rearrangement proceeding through a four-membered ring. It was also found that under certain conditions the amidyl radical produced by cleavage of the four-membered ring intermediate can undergo fragmentation to give an isocyanate. Such fragmentations are unprecedented at temperatures corresponding to refluxing benzene or chlorobenzene.

AB - (Chemical Equation Presented) Radicals derived from N-(α-xanthyl) acetanilides or N-(α-xanthyl)acetylaminopyridines possessing a substituent next to the nitrogen undergo a hitherto undocumented Smiles rearrangement proceeding through a four-membered ring. It was also found that under certain conditions the amidyl radical produced by cleavage of the four-membered ring intermediate can undergo fragmentation to give an isocyanate. Such fragmentations are unprecedented at temperatures corresponding to refluxing benzene or chlorobenzene.

U2 - 10.1021/ol051568l

DO - 10.1021/ol051568l

M3 - Article

AN - SCOPUS:24044451193

SN - 1523-7060

VL - 7

SP - 3817

EP - 3820

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

An unusual radical smiles rearrangement

Abstract

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